EP1557724B1 - Photoconductive imaging members - Google Patents

Photoconductive imaging members Download PDF

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Publication number
EP1557724B1
EP1557724B1 EP05100275A EP05100275A EP1557724B1 EP 1557724 B1 EP1557724 B1 EP 1557724B1 EP 05100275 A EP05100275 A EP 05100275A EP 05100275 A EP05100275 A EP 05100275A EP 1557724 B1 EP1557724 B1 EP 1557724B1
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EP
European Patent Office
Prior art keywords
layer
imaging member
charge transport
comprised
photoconductive imaging
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EP05100275A
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German (de)
English (en)
French (fr)
Other versions
EP1557724A1 (en
Inventor
Yuhua Tong
Satchidanand Mishra
Anthony M. Horgan
John F. Yanus
Dale S. Renfer
Robert C. U. Yu
Markus R. Silvestri
Cindy C. Chen
Lanhui Zhang
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Xerox Corp
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Xerox Corp
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Publication of EP1557724A1 publication Critical patent/EP1557724A1/en
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Publication of EP1557724B1 publication Critical patent/EP1557724B1/en
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/056—Polyesters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0532—Macromolecular bonding materials obtained by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/0546—Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0592—Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity

Definitions

  • This invention is generally directed to imaging members, and more specifically, the present invention is directed to single and multi-layered photoconductive imaging members with a hole blocking layer, which is typically a thin crosslinked silane coating, or an undercoat layer (UCL) comprised of, for example, a metal oxide, such as titanium oxide dispersed in a phenolic resin/phenolic resin blend or a phenolic resin/phenolic compound blend, and which layer can be deposited on a supporting substrate; a charge generation layer and a charge transport layer which contains a polymeric acid or a copolymer solid acid.
  • the photoconductive imaging members can be in a number of different forms, such as in a rigid form, a drum configuration, a web, a flexible belt configuration, which may be seamed or seamless.
  • the hole blocking layer in contact with the supporting substrate can be situated between the supporting substrate and the photogenerating layer, which is comprised, for example, of the photogenerating pigments of US-A-5,482,811 , especially Type V hydroxygallium phthalocyanine, and generally metal free phthalocyanines, metal phthalocyanines, perylenes, titanyl phthalocyanines, selenium, selenium alloys, azo pigments, squaraines.
  • the charge transport layer comprised of charge transport materials and binders is doped by solid acids to achieve high application performance.
  • the imaging members of the present invention in embodiments exhibit excellent photosensitivity; desirable low dark decay characteristics; steep photo induced discharge curves; low discharge residuals and substantially little or no cycle up is needed; cyclic/environmental stability; low and excellent V low , that is the surface potential of the imagine member subsequent to a certain light exposure, and which V low is 25 to 100 volts lower than, for example, a comparable imaging member; low depletion potentials; high photoinduced discharge curve sensitivity.
  • the photoresponsive, or photoconductive imaging members can be negatively charged when the photogenerating layers are situated between the charge transport layer and the hole blocking layer deposited on the substrate.
  • the layered photoconductive imaging members of the present invention can be selected for a number of different known imaging and printing processes including, for example, electrophotographic imaging processes, especially xerographic imaging and printing processes wherein charged latent images are rendered visible with toner compositions of an appropriate charge polarity.
  • the imaging members are in embodiments sensitive in the wavelength region of, for example, from 500 to 900 nanometers, and in particular from 650 to 850 nanometers, thus diode lasers can be selected as the light source.
  • the imaging members of this invention are useful in color xerographic applications, particularly high-speed color copying and printing processes.
  • US-A-4477547 discloses an electrophotographic photosensitive material comprising a conductive support having provided thereon, in the following order, a charge-generating layer (CGL) and a charge transport layer (CTL).
  • the CGL contains a charge carrier-generating substance and a binder, which comprises a polyamide resin and a high molecular weight compound.
  • the charge carrier-generating substances include organic pigments.
  • Suitable high molecular weight compounds comprise styrene-maleic anhydride copolymers, maleic acid ester resins, vinyl acetate-crotonic acid copolymers, vinyl acetate-maleic anhydride copolymers, acrylic acid resins, (meth)acrylic acid-(meth)acrylic acid ester copolymers, styrene-(meth)acrylic acid copolymers, and phthalic acid-maleic anhydride copolymers.
  • the CTL comprises a charge carrier transport substance and a binder containing a high molecular weight compound.
  • Examples of the charge carrier transport substances include aromatic tertiary amino compounds, aromatic tertiary diamino compounds, aromatic tertiary triamino compounds, condensates of aldehydes and aromatic amines, heterocyclic compounds, etc.
  • the high molecular weight compounds used in the CTL correspond to those, which are used in the CGL.
  • Electrophotographic photosensitive materials comprising a support, a CGL, and a CTL are also known from JP-A-06-051546 , JP-A-06-075387 , JP-A-59-166969 , JP-A-01-261659 , US-A-4559285 , and US-A-6287737 .
  • US-A-5681678 , and US-A-5725985 disclose electrophotographic photosensitive materials comprising a support, a CGL, and a CTL.
  • the CGL contains photoconductive particles dispersed in a polymer matrix, the matrix comprising a polymeric film-forming reaction product of at least vinyl chloride, vinyl acetate, and a hydroxyalkyl acrylate.
  • the CTL comprises a binder such as a polycarbonate resin, a polyvinylcarbazole resin, a polyester resin, a polyarylate resin, a polyacrylate resin, a polyether resin, or a polysulfone resin.
  • the present invention provides a photoconductive imaging member comprised of a photogenerating layer and a charge transport layer, wherein the charge transport layer contains a polymeric solid acid being a compound of the Formula (I) or (II): wherein x 1 , x 2 , x 3 and x 4 represent the molar percentage of each component in the polymer, and wherein the sum of x 1 , x 2 , x 3 and x 4 is equal to 1; wherein x 1 , x 2 , and x 3 represent the molar percentage of each component in the polymer, and the sum of x 1 , x 2 , and x 3 is equal to 1.
  • Another feature of the present invention relates to the provision of layered photoresponsive imaging members, which are responsive to near infrared radiation of from 700 to 900 nanometers.
  • Another feature of the present invention relates to the provision of layered photoresponsive imaging members with mechanically robust and solvent resistant hole blocking layers.
  • imaging members containing hole blocking polymer layers comprised of titanium oxide and a phenolic compound/phenolic resin blend, or a low molecular weight phenolic resin/phenolic resin blend, and which phenolic compounds containing at least two, and more specifically, two to ten phenolic groups or low molecular weight phenolic resins with a weight average molecular weight ranging from 500 to 2,000, and which components can interact with and consume formaldehyde and other phenolic precursors within the phenolic resin effectively, thereby chemically modifying the curing processes for such resins and permitting, for example, a hole blocking layer with excellent efficient electron transport, and which usually results in a desirable lower residual potential and V low .
  • a hole blocking layer comprised of titanium oxide, a phenolic resin/phenolic compound(s) blend or phenolic resin(s)/phenolic resin blend comprised of a first linear, or a first nonlinear phenolic resin, and a second phenolic resin or phenolic compounds containing at least 2, such as 2 to 12, 2 to 10, 3 to 8, 4 to 7, phenolic groups, and which blocking layer is applied to a drum of, for example, aluminum, and cured at a high temperature of, for example, from 135°C to 165°C.
  • a photoconductive imaging member of claim 1 comprised of a photogenerating layer and a charge transport layer, and wherein the charge transport layer contains a polymeric solid acid; a member comprised of a supporting substrate, a photogenerating layer, and a charge transport layer, and wherein the charge transport layer contains a copolymeric solid acid; a photoconductive imaging member comprised of a supporting substrate, an optional hole blocking layer, a photogenerating layer, and a charge transport layer, and wherein the charge transport layer contains a polymeric solid acid of poly(vinyl chloride-co-vinyl acetate-co-maleic acid), or poly(vinyl chloride-co-vinyl acetate-co-2-hydroxypropyl acrylate-co-maleic acid); a photoconductive imaging member wherein the hole blocking layer is of a thickness of 0.01 to 30 microns, and more specifically, is of a thickness of 1 to 8 microns; a photoconductive imaging member comprised in sequence of a supporting substrate,
  • MYLAR ® a commercially available polyethylene terephthalate polymer in the form of a flexible web or belt
  • MYLAR ® is provided with a conductive titanium surface, or a layer of an organic or inorganic material having a semiconductive surface layer, such as indium tin oxide, or aluminum arranged thereon, or a conductive material inclusive of aluminum, chromium, nickel, brass
  • the substrate may be flexible, seamless, rigid, or other suitable forms, and may have a number of many different configurations, such as for example, a plate, a cylindrical drum, a scroll, an endless flexible seamed belt.
  • the substrate is in the form of a seamless flexible belt.
  • the thickness of the substrate layer depends on many factors, including economical considerations, thus this layer may be of substantial thickness, for example over 3,000 microns, or such as from 400 to 700 microns used generally for rigid imaging members fabrication. Otherwise, the substrate may be of minimum thickness for flexibility provided there are no significant adverse effects on the resulting flexible imaging member. In embodiments, the thickness of this substrate layer is from 75 microns to 300 microns for fabrication of flexible imaging member belts.
  • the hole blocking layer when present can be applied directly over the conductive surface of the substrate, and wherein the hole blocking layer can be comprised of a number of suitable components, such as a crosslinked gamma amino propyl triethoxy silane having a thickness of 0.01 micron and 0.2 micron; a metal oxide dispersed in a blend of a phenolic compound and a phenolic resin, or a blend of two phenolic resins wherein the first resin possesses a weight average molecular weight of from 500 to 2,000, and the second resin possesses a weight average molecular weight of from 2,000 to 20,000.
  • suitable components such as a crosslinked gamma amino propyl triethoxy silane having a thickness of 0.01 micron and 0.2 micron; a metal oxide dispersed in a blend of a phenolic compound and a phenolic resin, or a blend of two phenolic resins wherein the first resin possesses a weight average molecular weight of from 500 to 2,000, and the
  • hole blocking layer components are titanium oxide, a dopant, such as a silicon oxide, a phenolic compound or compounds containing at least 2, preferably 2 to 10 phenolic groups, such as bisphenol S and/or a phenolic resin having a weight average molecular weight of from 500 to 2000, and a known phenolic resin, reference for example US-A-6,177, 219 .
  • the hole blocking layer is, for example, comprised of the components illustrated herein, and more specifically, from 20 weight percent to 80 weight percent, from 55 weight percent to 65 weight percent of a metal oxide, such as TiO 2 , from 20 weight percent to 70 weight percent, more specifically, from 25 weight percent to 50 weight percent of a phenolic resin, from 2 weight percent to 20 weight percent, more specifically, from 5 weight percent to 15 weight percent of a phenolic compound preferably containing at least two phenolic groups, such as bisphenol S, and from 2 weight percent to 15 weight percent, more specifically, from 4 weight percent to 10 weight percent of a plywood suppression dopant, such as SiO 2 .
  • the hole blocking layer coating dispersion can, for example, be prepared as follows.
  • the metal oxide/phenolic, resin dispersion is first prepared by ball milling or dynomilling until the median particle size of the metal oxide in the dispersion is less than 10 nanometers, for example from 5 to 9.
  • a phenolic compound and dopant are added followed by mixing.
  • the hole blocking layer coating dispersion can be applied by dip coating or web coating, and the layer can be thermally cured after coating.
  • the hole blocking layer resulting is, for example, of a thickness of from 0.01 micron to 30 microns, and more specifically, from 0.1 micron to 8 microns.
  • phenolic resins include formaldehyde polymers with phenol, p-tert butylphenol, cresol, such as VARCUM TM 29159 and 29101 (OxyChem Company) and DURITE TM 97 (Borden Chemical), formaldehyde polymers with ammonia, cresol and phenol, such as VARCUM TM 29112 (OxyChem, Company), formaldehyde polymers with 4,4'-(1-methylethylidene) bisphenol, such as VARCUM TM 29108 and 29116 (OxyChem Company), formaldehyde polymers with cresol and phenol, such as VARCUM TM 29457 (OxyChem Company), DURITE TM SD-423A, SD-422A (Borden Chemical), or formaldehyde polymers with phenol and p-tert -butylphenol, such as DURITE TM ESD 556C (Border Chemical).
  • VARCUM TM 29159 and 29101 Ox
  • Examples of specific solid polymeric acids are poly(vinyl chloride-co-vinyl acetate-co-maleic acid) (VMCH ® ), or poly(vinyl chloride-co-vinyl acetate-co-2-hydroxypropyl acrylate-co-maleic acid) with a M w of, for example, from 500 to 100,000, a M n of from 300 to 90,000, and yet more specifically, a M w of from 1,000 to 50,000 and a M n of from 800 to 40,000.
  • the amount of the solid acid present in the charge transport layer is, for example, from 0.01 to 20 percent by weight, and more specifically, from 0.1 to 5 percent by weight.
  • the charge transport layer in addition to containing charge transport components, resin binder and a solid acid may also include an antioxidant such as pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) (IRGANOX TM 1010) in an amount of, for example, from 1 to 15 weight percent based on the total weight of the layer components.
  • the charge transport layer may comprise a dual layer of a thickness of from 10 to 50 with each layer or one layer containing a solid acid dopant and the antioxidant in both layers; alternatively, the solid acid and antioxidant may be present only in the top charge transport layer.
  • 0.0001 to 10 microns size inorganic or organic fillers may also be added to the top charge transport layer to achieve filter reinforcement to provide excellent wear resistance, examples of fillers being silica, metal oxides, silicates, TEFLON ® , stearates, waxy polyethylene particles, salts of fatty acids and/or an overcoat protective layer can be utilized to improve resistance of the photoreceptor to abrasion.
  • an anticurl backing layer may be applied to the surface of the substrate opposite to that bearing the photoconductive layer to provide flatness and/or abrasion resistance where a web configuration photoreceptor is fabricated.
  • the photogenerating layer which can, for example, be comprised of hydroxygallium phthalocyanine Type V, is in embodiments comprised of, for example, about 60 weight percent of Type V and about 40 weight percent of a resin binder like polyvinylchloride vinylacetate copolymer such as VMCH (Dow Chemical).
  • a resin binder like polyvinylchloride vinylacetate copolymer such as VMCH (Dow Chemical).
  • the photogenerating layer can contain known photogenerating pigments, such as metal phthalocyanines, metal free phthalocyanines, alkylhydroxyl gallium phthalocyanine, hydroxygallium phthalocyanines, perylenes, especially bis(benzimidazo)perylene, titanyl phthalocyanines, and more specifically, vanadyl phthalocyanines, Type V hydroxygallium phthalocyanines, and inorganic components such as selenium, selenium alloys, and trigonal selenium.
  • the photogenerating pigment can be dispersed in a resin binder similar to the resin binders selected for the charge transport layer, or alternatively no resin binder is present.
  • the thickness of the photogenerator layer depends on a number of factors, including the thicknesses of the other layers and the amount of photogenerator material contained in the photogenerating layers. Accordingly, this layer can be of a thickness of, for example, from 0.05 micron to 10 microns, and more specifically, from 0.25 micron to 2 microns, and wherein, for example, the photogenerator component is present in an amount of from 30 to 75 percent by volume.
  • the maximum thickness of this layer in embodiments is dependent primarily upon factors, such as the desired photosensitivity, the achievement of certain electrical properties, the amount of pigment dispersion, and mechanical considerations.
  • the photogenerating layer binder resin present in various suitable amounts may be selected from a number of known polymers such as poly(vinyl butyral), poly(vinyl carbazole), polyesters, polycarbonates, poly(vinyl chloride), polyacrylates and methacrylates, copolymers of vinyl chloride and vinyl acetate, phenolic resins, polyurethanes, poly(vinyl alcohol), polyacrylonitrile, polystyrene. It is desirable to select a coating solvent that does not substantially disturb or adversely affect the other previously coated layers of the device.
  • the provision of the photogenerator layer in embodiments of the present invention can be accomplished with spray, dip or wire-bar methods such that the final dry thickness of the photogenerator layer is, for example, from 0.01 to 30 microns, and more specifically, from 0.1 to 15 microns after being dried at, for example, 40°C to 150°C for 15 to 90 minutes.
  • polymeric binder materials that can be selected for the photogenerator layer are as indicated herein, and include those polymers as disclosed in US-A-3,121,006 .
  • the effective amount of polymer binder that is utilized in the photogenerator layer ranges from 0 to 95 percent by weight, and preferably from 25 to 60 percent by weight of the photogenerator layer.
  • adhesive layers usually formed to be in contact with the hole blocking layer and the photogenerator layer there can be selected various known substances inclusive of polyesters, polyamides, poly(vinyl butyral), poly(vinyl alcohol), polyurethane and polyacrylonitrile.
  • This layer is, for example, of a thickness of from 0.001 micron to 1 micron.
  • this layer may contain effective suitable amounts, for example from 1 to 10 weight percent, of conductive and nonconductive particles, such as zinc oxide, titanium dioxide, silicon nitride, carbon black, to provide, for example, in embodiments of the present invention further desirable imaging member electrical and optical properties.
  • the charge transport layer which generally is of a thickness of from 5 microns to 75 microns, and more specifically, of a thickness of from 10 microns to 40 microns, can be comprised of known charge transporting materials and to be later developed materials, and which layer, for example, can be comprised of the polymeric solid acid illustrated herein, and molecules of the following formula dispersed in a highly insulating and transparent polymer binder, wherein X is an alkyl group, an alkoxy, a halogen, or mixtures thereof, and especially those substituents selected from the group consisting of Cl and CH 3 .
  • Examples of specific aryl, amines are N,N' -diphenyl- N,N'- bis(alkylphenyl)-1,1-biphenyl-4,4'-diamine wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, butyl, hexyl, and N,N'- diphenyl- N,N' -bis(halophenyl)-1,1'-biphenyl-4,4'-diamine wherein the halo substituent is preferably a chloro substituent.
  • Other known charge transport layer molecules can be selected, reference for example, US-A-4,921,773 and US-A-4,464,450 .
  • binder materials for the transport layer include components, such as those described in US-A-3,121,006 .
  • polymer binder materials include polycarbonates, acrylate polymers, vinyl polymers, cellulose polymers, polyesters, polysiloxanes, polyamides, polyurethanes, poly(cyclo olefins), and epoxies as well as block, random or alternating copolymers thereof.
  • Preferred electrically inactive binders are comprised of polycarbonate resins with a molecular weight of from 20,000 to 100,000 or with a molecular weight M w of from 50,000 to 100,000 being particularly preferred.
  • the transport layer contains from 10 to 75 percent by weight of the charge transport component, and more specifically, from 35 percent to 50 percent of this material.
  • the imaging method involves the same steps with the exception that the exposure step can be accomplished with a laser device or image bar.
  • An electrophotographic imaging member web stock was prepared by providing a 0.02 micrometer thick titanium layer coated on a substrate of a biaxially oriented polyethylene naphthalate substrate (KADALEX TM , available from ICI Americas, Inc.) having a thickness of 3.5 mils (89 micrometers).
  • the titanized KADALEX TM substrate was coated with a blocking layer solution containing a mixture of 10 grams of gamma aminopropyltriethoxy silane, 10.1 grams of distilled water, 3 grams of acetic acid, 684.8 grams of 200 proof denatured alcohol and 200 grams of heptane.
  • This wet coating layer was then allowed to dry for 5 minutes at 135°C in a forced air oven to remove the solvents from the coating and effect the formation of a crosslinked silane blocking layer.
  • the resulting blocking layer was of an average dry thickness of 0.05 micrometer as measured with an ellipsometer.
  • An adhesive interface layer was then deposited by applying to the blocking layer a wet coating solution containing 5 percent by weight of the polyester MOR-ESTER 49,000 ® , having a weight average molecular weight of about 70,000, available from Morton International, and based on the total weight of the solution in a 70:30 volume ratio mixture of tetrahydrofuran/cyclohexanone.
  • the adhesive interface layer was allowed to dry for 5 minutes at 135°C in a forced air oven.
  • the resulting adhesive interface layer had a dry thickness of 0.065 micrometer.
  • a slurry coating solution of 40 percent by volume hydroxygallium phthalocyanine and 60 percent by volume poly(4,4'-diphenyl-1,1'-cyclohexane carbonate (PCZ-200TM, available from Mitsubishi Gas Chemical) dispersed in tetrahydrofuran was extrusion coated onto this adhesive interface layer.
  • the coated member was dried at 135°C in a forced air oven to form a dry photogenerating layer having a thickness of 0.4 micrometer.
  • HTMI transport layers
  • the hole transport compound N,N'-diphenyl-N,N'-bis(3-methyl-phenyl)-(1,1'-biphenyl)-4,4'-diamine wherein X is a methyl group attached to the meta position the weight percent illustrated herein (based on total solids) polycarbonate resin MAKROLON ® 5705, a poly(4,4'-isopropylidene-diphenylene) carbonate available from Wegricken Bayer A.G.
  • the weight percent illustrated herein of the antioxidant IRGANOX 1010 ® pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate) available from Ciba Spezialitatenchemie AG, and 0 (zero) and 1 weight percent UCARMAG 527
  • each photoreceptor sheet to be evaluated was mounted on a cylindrical aluminum drum substrate which was rotated on a shaft.
  • the devices were charged by a corotron mounted along the periphery of the drum.
  • the surface potential was measured as a function of time by capacitively coupled voltage probes placed at different locations around the shaft. The probes were calibrated by applying known potentials to the drum substrate.
  • Each photoreceptor sheet on the drum was exposed to a light source located at a position near the drum downstream from the corotron. As the drum was rotated, the initial (pre-exposure) charging potential was measured by voltage probe 1.
  • Table 2 indicates the background potentials of probe 2 at 10 ergs/cm 2 , the exposure energy to discharge the photoreceptors to half of their initial potentials V 0 , and the dark decay for one second at an initial potential of about 900V.
  • Table 3 provides the same parameters as in Table 2 for the same devices that have been electrically fatigued for 10,000 cycles.
  • Example I Four of the photogenerator layers of Example I were coated with transport layers of 45 weight percent (based on total solids) of the hole transport compound N,N-di-(3,4-dimethylphenyl)4-biphenylamine X (as illustrated in Table 4) weight percent (based on total solids) of the polycarbonate resin MAKROLON ® 5705, a poly(4,4'-isopropylidene-diphenylene) carbonate available from Wegricken Bayer A.G., Y weight percent of the antioxidant IRGANOX 1010 ® , pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate) available from Ciba Spezialitatenchemie AG, and Z weight percent of UCARMAG 527 ® available from Union Carbide, applied as a solution in methylene chloride at 17 weight percent.
  • the coated devices were heated in an oven maintained at from 40°C to 100°C over 30 minutes to form a charge transport layer having a thickness of 25 micrometers.
  • the composition of the four transport layers are shown in Table 4. TABLE 4 DEVICE # MAKROLON WT% HTM WT% IRGANOX 1010 ® UCARMAG 527 ® 3 55% 45% 0 0 4 54% 45% 0 1% 5 49% 45% 6% 0 6 48% 45% 6% 1%
  • Example IV The flexible photoreceptor sheets prepared as described in Example IV were tested in the same manner as in Example II for their xerographic sensitivity and cyclic stability in a scanner.
  • Table 5 provides the background potentials of probe 2 at 10 ergs/cm 2 , the exposure energy to discharge the photoreceptors to half of their initial potentials V 0 , and the dark decay for one second at an initial potential of about 900V.
  • Table 6 provides the same parameters as in Table 5 for the same devices that have been electrically fatigued for 10,000 cycles.
  • DEVICE # POTENTIAL [V] AT 10ERGS/CM 2 @ 10K CYCLES RESIDUAL POTENTIAL AFTER ERASE [V] AT 10K CYCLES EXPOSURE ENERGY FOR V 0 /2 [ERGS/CM 2 ] @ 10K CYCLES 1S DARK DECAY @ V 900V AND 10K CYCLES 3 133 87 1.3 160 4 14 3 1.14 84 5 250 199 1.45 52 6 17 4 1.14 78
  • Devices 4 and 6 that contained UCARMAG 527 ® possessed lower background voltages, excellent residual voltage, and excellent stability discharge characteristics. The dark decay was not detrimentally affected.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
EP05100275A 2004-01-22 2005-01-18 Photoconductive imaging members Expired - Lifetime EP1557724B1 (en)

Applications Claiming Priority (2)

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US762669 2004-01-22
US10/762,669 US7045262B2 (en) 2004-01-22 2004-01-22 Photoconductive imaging members

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EP1557724A1 EP1557724A1 (en) 2005-07-27
EP1557724B1 true EP1557724B1 (en) 2012-03-14

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US7267917B2 (en) * 2004-09-21 2007-09-11 Xerox Corporation Photoreceptor charge transport layer composition
US7348114B2 (en) * 2005-05-11 2008-03-25 Xerox Corporation Photoconductive members
US7462431B2 (en) * 2005-05-12 2008-12-09 Xerox Corporation Photoreceptors
JP5266693B2 (ja) * 2007-09-07 2013-08-21 富士ゼロックス株式会社 ガリウムフタロシアニン結晶及びその製造方法、感光体、プロセスカートリッジ、並びに、画像形成装置
US7811729B2 (en) * 2008-12-11 2010-10-12 Xerox Corporation Imaging member
US8057974B2 (en) * 2008-12-11 2011-11-15 Xerox Corporation Imaging member
US8304151B2 (en) * 2009-11-30 2012-11-06 Xerox Corporation Corona and wear resistant imaging member
US8394560B2 (en) * 2010-06-25 2013-03-12 Xerox Corporation Imaging members having an enhanced charge blocking layer
MX380676B (es) * 2013-04-29 2025-03-12 Essilor Int Potenciadores de la tincion para la tincion de un recubrimiento duro.
US10146150B2 (en) * 2016-06-01 2018-12-04 Canon Kabushiki Kaisha Process cartridge, image forming apparatus, image forming method

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4265990A (en) 1977-05-04 1981-05-05 Xerox Corporation Imaging system with a diamine charge transport material in a polycarbonate resin
JPS58118658A (ja) 1982-01-07 1983-07-14 Mitsubishi Paper Mills Ltd 積層平版印刷版の製造法
JPS59166969A (ja) 1983-03-14 1984-09-20 Mitsubishi Paper Mills Ltd 積層型平版印刷版の製造法
DE3324090A1 (de) 1983-07-05 1985-01-17 Basf Ag, 6700 Ludwigshafen Elektrophotographische aufzeichnungsmaterialien mit verbesserter photoempfindlichkeit
US4555463A (en) 1984-08-22 1985-11-26 Xerox Corporation Photoresponsive imaging members with chloroindium phthalocyanine compositions
US4587189A (en) 1985-05-24 1986-05-06 Xerox Corporation Photoconductive imaging members with perylene pigment compositions
JPH01261659A (ja) 1988-04-12 1989-10-18 Mitsubishi Paper Mills Ltd 積層型平版印刷版の製造法
US4921769A (en) 1988-10-03 1990-05-01 Xerox Corporation Photoresponsive imaging members with polyurethane blocking layers
DE3835520A1 (de) * 1988-10-19 1990-04-26 Basf Ag Panchromatisches elektrophotographisches aufzeichnungselement
JP2565400B2 (ja) * 1989-06-20 1996-12-18 財團法人 工業技術研究院 ポリマー結合剤としてスチレンー無水マレイン酸コポリマーを使用する電子写真感光体
JPH0675387A (ja) 1991-07-19 1994-03-18 Ricoh Co Ltd 電子写真用感光体
JPH0651546A (ja) * 1991-07-19 1994-02-25 Ricoh Co Ltd 電子写真用感光体
US5473064A (en) 1993-12-20 1995-12-05 Xerox Corporation Hydroxygallium phthalocyanine imaging members and processes
US5482811A (en) 1994-10-31 1996-01-09 Xerox Corporation Method of making hydroxygallium phthalocyanine type V photoconductive imaging members
US5521043A (en) 1995-05-05 1996-05-28 Xerox Corporation Hydroxygallium phthalocyanine pigments with block copolymer binders
US6012645A (en) * 1995-07-17 2000-01-11 Chaska Chemical Company Floor cleaning machine
US5725985A (en) 1997-01-21 1998-03-10 Xerox Corporation Charge generation layer containing mixture of terpolymer and copolymer
US5681678A (en) 1997-01-21 1997-10-28 Xerox Corporation Charge generation layer containing hydroxyalkyl acrylate reaction product
US6015645A (en) 1998-05-29 2000-01-18 Xerox Corporation Photoconductive imaging members
US6177219B1 (en) 1999-10-12 2001-01-23 Xerox Corporation Blocking layer with needle shaped particles
US6156468A (en) 2000-05-22 2000-12-05 Xerox Corporation Blocking layer with light scattering particles having rough surface
US6255027B1 (en) 2000-05-22 2001-07-03 Xerox Corporation Blocking layer with light scattering particles having coated core
US6287737B1 (en) 2000-05-30 2001-09-11 Xerox Corporation Photoconductive imaging members

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US7045262B2 (en) 2006-05-16
JP4693426B2 (ja) 2011-06-01
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